A Convenient Synthesis of Primary Amines Using Sodium Diformylamide as A Modified Gabriel Reagent
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (02) , 122-124
- https://doi.org/10.1055/s-1990-26805
Abstract
Sodium diformylamide (1) was used as a convenient substitute for phthalimide in the Gabriel synthesis of primary amines. Reagent 1 undergoes smooth N-alkylation with alkyl halides or p-toluenesulfonates 2 in acetonitrile or dimethylformamide to give the corresponding N,N-diformylalkylamines 3 in good yields, except with alkylating agents which are susceptible to base-catalyzed elimination. The formyl group of 3 can be easily removed by hydrochloric acid to give the corresponding alkylamine hydrochlorides 5 or free alkylamines 4.Keywords
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